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Article: Intramolecular C-N bond formation reactions catalyzed by ruthenium porphyrins: Amidation of sulfamate esters and aziridination of unsaturated sulfonamides

TitleIntramolecular C-N bond formation reactions catalyzed by ruthenium porphyrins: Amidation of sulfamate esters and aziridination of unsaturated sulfonamides
Authors
Issue Date2004
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc
Citation
Journal Of Organic Chemistry, 2004, v. 69 n. 11, p. 3610-3619 How to Cite?
AbstractRuthenium porphyrins [Ru(F20-TPP)(CO)] (F20-TPP = 5,10,15,20-tetrakis(pentafluorophenyl)porphyrinato dianion) and [Ru(Por*)(CO)] (Por* = 5,10,15,20-tetrakis[(1S,4R,5R,8S)-1,2,3,4,5,6,7,8-octahydro-1,4:5, 8-dimethanoanthracen-9-yl]porphyrinato dianion) catalyzed intramolecular amidation of sulfamate esters p-X-C6H4(CH 2)2OSO2NH2 (X = Cl, Me, MeO), XC6H4(CH2)3OSO2NH 2 (X = p-F, p-MeO, m-MeO), and Ar(CH2)2OSO 2NH2 (Ar = naphthalen-1-yl, naphthalen-2-yl) with PhI(OAc)2 to afford the corresponding cyclic sulfamidates in up to 89% yield with up to 100% substrate conversion; up to 88% ee was attained in the asymmetric intramolecular amidation catalyzed by [Ru(Por*)(CO)]. Reaction of [Ru(F20-TPP)(CO)] with PhI=NSO2OCH 2CCl3 (prepared by treating the sulfamate ester Cl 3CCH2OSO2NH2 with PhI(OAc) 2) afforded a bis(imido)ruthenium(VI) porphyrin, [Ru VI(F20-TPP)(NSO2OCH2CCl 3)2], in 60% yield. A mechanism involving reactive imido ruthenium porphyrin intermediate was proposed for the ruthenium porphyrin-catalyzed intramolecular amidation of sulfamate esters. Complex [Ru(F20-TPP)(CO)] is an active catalyst for intramolecular aziridination of unsaturated sulfonamides with PhI(OAc)2, producing corresponding bicyclic aziridines in up to 87% yield with up to 100% substrate conversion and high turnover (up to 2014).
Persistent Identifierhttp://hdl.handle.net/10722/69114
ISSN
2015 Impact Factor: 4.785
2015 SCImago Journal Rankings: 2.095
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorLiang, JLen_HK
dc.contributor.authorYuan, SXen_HK
dc.contributor.authorHuang, JSen_HK
dc.contributor.authorChe, CMen_HK
dc.date.accessioned2010-09-06T06:10:42Z-
dc.date.available2010-09-06T06:10:42Z-
dc.date.issued2004en_HK
dc.identifier.citationJournal Of Organic Chemistry, 2004, v. 69 n. 11, p. 3610-3619en_HK
dc.identifier.issn0022-3263en_HK
dc.identifier.urihttp://hdl.handle.net/10722/69114-
dc.description.abstractRuthenium porphyrins [Ru(F20-TPP)(CO)] (F20-TPP = 5,10,15,20-tetrakis(pentafluorophenyl)porphyrinato dianion) and [Ru(Por*)(CO)] (Por* = 5,10,15,20-tetrakis[(1S,4R,5R,8S)-1,2,3,4,5,6,7,8-octahydro-1,4:5, 8-dimethanoanthracen-9-yl]porphyrinato dianion) catalyzed intramolecular amidation of sulfamate esters p-X-C6H4(CH 2)2OSO2NH2 (X = Cl, Me, MeO), XC6H4(CH2)3OSO2NH 2 (X = p-F, p-MeO, m-MeO), and Ar(CH2)2OSO 2NH2 (Ar = naphthalen-1-yl, naphthalen-2-yl) with PhI(OAc)2 to afford the corresponding cyclic sulfamidates in up to 89% yield with up to 100% substrate conversion; up to 88% ee was attained in the asymmetric intramolecular amidation catalyzed by [Ru(Por*)(CO)]. Reaction of [Ru(F20-TPP)(CO)] with PhI=NSO2OCH 2CCl3 (prepared by treating the sulfamate ester Cl 3CCH2OSO2NH2 with PhI(OAc) 2) afforded a bis(imido)ruthenium(VI) porphyrin, [Ru VI(F20-TPP)(NSO2OCH2CCl 3)2], in 60% yield. A mechanism involving reactive imido ruthenium porphyrin intermediate was proposed for the ruthenium porphyrin-catalyzed intramolecular amidation of sulfamate esters. Complex [Ru(F20-TPP)(CO)] is an active catalyst for intramolecular aziridination of unsaturated sulfonamides with PhI(OAc)2, producing corresponding bicyclic aziridines in up to 87% yield with up to 100% substrate conversion and high turnover (up to 2014).en_HK
dc.languageengen_HK
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/jocen_HK
dc.relation.ispartofJournal of Organic Chemistryen_HK
dc.titleIntramolecular C-N bond formation reactions catalyzed by ruthenium porphyrins: Amidation of sulfamate esters and aziridination of unsaturated sulfonamidesen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0022-3263&volume=69&spage=3610&epage=3619&date=2004&atitle=Intramolecular+C-N+bond+formation+reactions+catalyzed+by+ruthenium+porphyrins:+amidation+of+sulfamate+esters+and+aziridination+of+unsaturated+sulfonamidesen_HK
dc.identifier.emailHuang, JS:jshuang@hkucc.hku.hken_HK
dc.identifier.emailChe, CM:cmche@hku.hken_HK
dc.identifier.authorityHuang, JS=rp00709en_HK
dc.identifier.authorityChe, CM=rp00670en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/jo0358877-
dc.identifier.pmid15152988-
dc.identifier.scopuseid_2-s2.0-2442704159en_HK
dc.identifier.hkuros94239en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-2442704159&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume69en_HK
dc.identifier.issue11en_HK
dc.identifier.spage3610en_HK
dc.identifier.epage3619en_HK
dc.identifier.isiWOS:000221624900002-
dc.publisher.placeUnited Statesen_HK
dc.identifier.scopusauthoridLiang, JL=7404541484en_HK
dc.identifier.scopusauthoridYuan, SX=7403272864en_HK
dc.identifier.scopusauthoridHuang, JS=7407192639en_HK
dc.identifier.scopusauthoridChe, CM=7102442791en_HK

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